Organosilane compounds

ABSTRACT

Novel compounds of formula ##STR1## or siloxane oligomers thereof, wherein x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl group containing 1 to 18 carbon atoms or an acyl group containing 1 to 4 carbon atoms, a is 0 to 2; c is 0 to 2 provided a+c does not exceed 2; R 1  is an alkyl group containing 1 to 4 carbon atoms; R 2  is an alkyl group containing 1 to 18 carbon atoms; b is 1 to 3; R 3  is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, a caboxy-substituted alkyl group containing 1 to 4 carbon atoms, 
     
         (C.sub.x H.sub.2x O).sub.m Z 
    
     where x, m, and Z are as defined above, or oxygen provided only one R 3  is oxygen; R 4  is an alkyl, aryl, or arylalkyl group containing 1 to 22 carbon atoms; X is halide; and Y is nitrogen, phosphorus, or sulfur are disclosed. The novel compounds are useful for inclusion in a detergent composition for imparting soil release benefits to metallic and vitreous surfaces washed or rinsed therewith.

BACKGROUND OF THE INVENTION

This invention relates to novel organosilane compounds.

Various quaternized substituted organosilane compounds are known. Forexample, British Pat. No. 686,068 discloses compounds having the generalformula

    [(R.sub.3 SiCH.sub.2).sub.a NR.sup.1.sub.b H.sub.4-a-b ]Y

where R is an alkyl, monocyclic aryl hydrocarbon or alkoxy radical, R¹is an alkyl, alicyclic hydrocarbon or monocyclic aryl hydrocarbonradical or hydroxy alkyl radical, a is 1 to 2, b is 0 to 3 with a+bbeing not greater than 4 and Y is an acid anion. British Pat. No.1,164,581 discloses compounds of the general formula

    [(RO).sub.a Si(CH.sub.3).sub.3-a CH.sub.2 N(CH.sub.3).sub.3 ].sup.+Br.sup.-

wherein R is an alkyl radical containing 1 to 6 carbon atoms or a phenylradical and a is 1 or 2. U.S. Pat. No. 3,730,701 discloses compounds ofthe formula

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3).sub.2 R R.sup.1

where R is an alkyl group containing 11 to 22 carbon atoms, and R¹ ishalide. These compounds are said to be useful as intermediates in theformation of organosilicon resins, catalysts and emulsifying agents(British Pat. No. 686,068), interfacial active agents and as modifiersfor organopolysiloxane resins and oils (British Pat. No. 1,164,581) andfor the control of algae (U.S. Pat. No. 3,730,701).

U.S. Pat. No. 2,955,127 discloses compounds of formula

    R.sub.2 N(O)C.sub.a H.sub.2a Si.sub.3

where R is a monovalent hydrocarbon group, a is at least 2, and Z is amonovalent hydrocarbon group, an alkoxy group, aryloxy group, hydroxygroup, siloxy group or a

    R.sub.2 N(O) C.sub.a H.sub.2a

group.

It has now been found that the novel compounds as hereindescribed areuseful as an additive to a detergent composition. Commonly assignedcopending Patent Applications "Organosilane-Containing DetergentComposition" and "Organosilane-Containing Anionic DetergentCompositions", both by Heckert and Watt, filed of even date, U.S. Ser.Nos. 570,534 and 576,533 respectively disclose detergent compositionscontaining a class of organosilanes. When metallic or vitreous surfacesare washed with a detergent composition containing the organosilane, athin polymeric coating of the organosilane is deposited upon the washedor rinsed surfaces. The polymerized coating imparts a soil releasebenefit to the surface, thereby making the surface easier to clean insubsequent washings.

It is an object of this invention to produce novel organosilanecompounds.

It is another object of this invention to produce organosilane compoundshaving utility in a detergent composition.

These and other objects will become apparent from the description tofollow.

As used herein all percentages and ratios are by weight unless otherwiseindicated.

SUMMARY OF THE INVENTION

An organosilane having the formula ##STR2##or siloxane oligomersthereof, wherein x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkylgroup containing 1 to 18 carbon atoms or an acyl group containing 1 to 4carbon atoms; a is 0 to 2; c is 0 to 2 provided a+c does not exceed 2;R₁ is an alkyl group containing 1 to 4 carbon atoms; R₂ is an alky1group containing 1 to 18 carbon atoms; b is 1 to 3; R₃ is an alkyl, arylor arylalkyl group containing 1 to 12 carbon atoms, acarboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m, and Z are as defined above, or oxygen provided only one R₃is oxygen; R₄ is an alkyl, aryl, or arylalkyl group containing 1 to 22carbon atoms; X is halide; and Y is nitrogen, phosphorus, or sulfur.

DETAILED DESCRIPTION OF THE INVENTION

This invention relates to organosilane compounds having the formula##STR3## or siloxane oligomers thereof wherein Z, x, m, a, c, R₁, R₂, b,R₃, R₄, Y and X are as defined immediately above. Preferably X ischloride or bromide, (a+c) is 2, R₂ is a methyl group, R₃ is an alkylgroup containing 1 to 4 carbon atoms and R₄ is an alkyl, aryl orarylalkyl group containing 6 to 12 carbon atoms.

It should be understood that R₃ in the above formula and formulas tofollow may be the same or different. It should be further understoodthat when Y is sulfur, there will be only one R₃. The 1 to 4 carbonatoms in the carboxy-substituted alkyl group is inclusive of thecarboxyl group. Also, when one R₃ is oxygen or, under basic conditions,the anion of a carboxylic acid substituted alkyl, the counter ion X⁻ isnot extant.

Compounds of the formula ##STR4## wherein b is 3, R₃ is an alkyl, arylor arylalkyl group, and Z, x, m, R₄, Y and X are defined as above areprepared by the following route:

    __________________________________________________________________________    X.sub.3 SiH    + CH.sub.2CHCH.sub.2 X                                                                      ##STR5##                                                                          X.sub.3 Si(CH.sub.2).sub.3 X                 (trihalosilane)  (allyl halide)  (gamma-halopropyltrihalosilane)              X.sub.3 Si(CH.sub.2).sub.3 X                                                                 + Z(OC.sub.x H.sub.2x).sub.m OH                                                             ##STR6##                                                                          [Z(OC.sub.x H.sub.2x).sub.m O].sub.3                                          Si(CH.sub.2).sub.3 X + 2HX                                                    [gamma-halopropyltris(polyalkylene-                                           oxy)silane]                                  [Z(OC.sub.x H.sub.2x)O].sub.3 Si(CH.sub.2).sub.3 X                                           + (R.sub.3).sub.1 or .sub.2 YR.sub.4                                                        ##STR7##                                                                           ##STR8##                                                 (tertiary amine,    [gamma-trialkylammoniopropyltris(polyalky                                     -                                                         tertiary phosphine, leneoxy)silane halide, gamma-trialkyl-                    or dialkylsulfide)  phosphoniopropyltris(polyalkyleneoxy)-                                        silane halide, or gamma-dialkylsulfonio-                                      1                                                                             propyltris(polyalkyleneoxy)silane            __________________________________________________________________________                                     halide]                                  

The trihalosilane (where the halogen is chloride or bromide) is reactedwith the allyl chloride at about 100° C. for from 4 to 10 hours in thepresence of a catalyst, e.g., chloroplatinic acid or platinum. Theresultant gammahalopropyltrihalosilane is reacted with a

    Z(OC.sub.x H.sub.2x).sub.m OH

compound to produce the gamma-halopropyltris(polyalkyleneoxy)silane. Atleast three equivalents of the

    Z(OC.sub.x H.sub.2x).sub.m OH

per equivalent of halo-propyltrihalosilane are added slowly to thesilane. The gamma-halopropyltrihalosilane may be dissolved in an inertsolvent, preferably hexane or pentane. (See W. Noll, "Chemistry andTechnology of Silanes", Academic Press, New York, 1968, page 81 for thealcoholysis of halosilanes.) One equivalent of thegamma-halopropyltris(polyalkyleneoxy)silane is reacted with oneequivalent of the tertiary amine, tertiary phosphine, or dialkylsulfideto produce the organosilane. An inert solvent, preferably of highdielectric constant, may be used. The reaction is carried out attemperatures of from 40° to 100° C. and a time of 2 to 10 hours for thereaction of the bromopropyltris(polyalkyleneoxy)silane and 120° to 140°C. for 2 to 20 hours for the reaction of thechloropropyltris(polyalkyleneoxy)silane.

The compounds of Formula I when at least one R₄ is a carboxy-substitutedalkyl group are prepared in the same manner except for the last reactionstep. Here, a tertiary amine, tertiary phosphine or dialkylsulfidehaving a carboxy-containing alkyl group(s) is reacted with the alpha,beta or gamma-haloalkyltris(polyalkyleneoxy)silane at 50° C. to 200° C.for 2 hours to 20 hours. Such carboxy-substituted tertiary amines,tertiary phosphines, and dialkylsulfides are produced by reacting

    R.sub.3 YHR.sub.4 or HYR.sub.4 (where Y is sulfur)

with

    X(CH.sub.2).sub.1-3 COOH

in the presence of base at elevated temperatures, e.g. 50° to 150° C.

The compounds of Formula I when at least one R₄ is

    (C.sub.x H.sub.2x O).sub.m Z

with x, m and Z as defined above are produced in the manner given aboveexcept for the last reaction. Thus, alpha-beta- andgamma-haloalkyltris(polyalkyleneoxy)silane is reacted with a tertiaryamine, tertiary phosphine, or dialkylsulfide where at least onesubstituent is

    (C.sub.x H.sub.2x O).sub.m Z

the reaction takes place at a temperature of 50° to 200° C. and a timeof from 2 to 10 hours.

Compounds of Formula I when one R₄ is oxygen are prepared by followingthe reactions outlined above up to the last reaction step. At thispoint, a dialkyl amine, dialkyl phosphine or alkylthiol is reacted withthe halosilane at 50° to 200° C. for from 4 to 10 hours and then withbase to produce an intermediate tertiary amine, phosphine, or dialkylsulfide. These intermediates are then reacted with H₂ O₂ at 20° C. to100° C. or preferably O₃ in an inert solvent at -80° C. to 20° C. toyield the organosilane.

When b is 2 in Formula I, a trihalovinylsilane of formula

    X.sub.3 SiCH=CH.sub.2

(which is commercially available) is reacted with hydrogen bromide inthe presence of peroxide and light to produce abeta-haloethyltrihalosilane. This compound is reacted with

    Z(OC.sub.x H.sub.2x).sub.m OH

and thereafter with an appropriate amine, phosphine, of sulfide in themanner discussed above for the preparation of the compounds of Formula Iwhen b is 3.

When b is 1 in Formula I, the starting reactant is a commerciallyavailable trihalomethylsilane of formula

    X.sub.3 SiCH.sub.3.

this silane is reacted with chlorine or, preferably a half mole ofbromine and a half mole of chlorine in the presence of light (such asprovided by an ordinary tungsten or fluorescent lamp). The resultantalpha-halomethyltrihalosilane is reacted with

    Z(OC.sub.x H.sub.2x).sub.m OH

and thereafter an appropriate amine, phosphine or sulfide in the mannerdiscussed above with the compounds of Formula I when b is 3.

When a is 1 or 2 and c is 0, the organosilane is prepared in a mannersimilar to the preparation of the compounds of Formula I except for thefact that the starting reactants (when b is 1, 2, or 3) all have a C₁₋₁₈alkyl group or two C₁₋₁₈ alkyl groups attached to the Si atom in placeof a halogen atom(s). The starting reactant is commercially availablewhen R₂ is CH₃. When R₂ is C₂ H₅ or greater, the compound is prepared byreacting a silane with an appropriate olefin. Thus,

    X.sub.3.sub.-a SiH.sub.1.sub.+a

is reacted with a C₂ to C₁₈ olefin to obtain the desired startingreactant. The remaining reaction steps and conditions for producing thedesired organosilane are essentially the same as for producing thecompounds of Formula I.

When a is 0 or 1 and c is 1 or 2 the organosilane is formed insubstantially the same manner as those of Formula I except that amixture of R₁ OH and

    Z(OC.sub.x H.sub.2x).sub.m OH

in the desired ratio is used in place of the

    Z(OC.sub.x H.sub.2x).sub.m OH

in the reaction with the haloalkyltrihalosilane.

Alternatively, the subject compounds are formed by reacting 3equivalents of R₁ OH with the haloalkyltrihalosilane and reacting theresultant compound with the amine, phosphine or sulfide to produce anorganosilane having three R₁ O groups attached to the silicon atoms.This compound is then heated with less than 3-a equivalents of

    (OC.sub.x H.sub.2x).sub.m OH

under conditions such that R₁ OH is removed from the system.

Exemplary compounds follow:

[Ch₃ (OC₂ H₄)O]₃ SiCH₂ N⁺(CH₃)₂ C₁₄ H₂₉ Cl⁻

[CH₃ (OC₂ H₄)₅ O]₂ CH₃ Si(CH₂)₃ N⁺(CH₂ COOH)₂ C₁₀ H₂₁ Cl⁻

[H(OC₃ H₆)₃ O]₃ SiCH₂ N⁺(C₂ H₄ OH) (C₃) C₁₂ H₂₅) Cl⁻

[H(OC₂ H₄)₁₈ O]₃ Si(CH₂)₂ N⁺(O)⁻(CH₃)C₁₈ H₃₇

[ch₃ co(oc₂ h₄)₁₀ o]₃ siCH₂ N⁺[(C₂ H₄ O)₁₄ H]₂ C₈ H₁₆ C₆ H₅ Cl⁻

[C₁₆ H₃₃ (OC₂ H₄)₈ O]₂ C₆ H₁₃ SiCH₂ N⁺[C₃ H₆ O)CH₃ ](CH₃)₂ Br⁻

[H(OC₄ H₈)₈ O]₃ SiCH₂ N⁺[(C₂ H₄ O)₄ COCH₃ ]₂ CH₃ Cl⁻

[C₆ H₁₃ (OC₂ H₄)₂ O]₃ Si(CH₂)₂ P⁺(CH₃)₂ C₁₀ H₂₁ Br⁻

[CH₃ (OC₃ H₆)₁₄ O]₃ SiCH₂ P⁺(C₂ H₄ COOH) (C₆ H₁₃)₂ Cl⁻

[C₂ H₅ (OC₂ H₄)O]₂ CH₃ Si(CH₂)₂ P⁺(C₄ H₈ OH) (CH₃)C₆ H₅ Cl⁻

[CH₃ (OC₂ H₄)₈ O]₃ SiCH₂ P⁺(O)⁻(CH₃)C₈ H₁₇

[c₂ h₅ oc(oc₂ h₄)₂ o]₃ si(CH₂)₃ P⁺[C₂ H₄ O)₈ H]₂ C₆ H₁₃ Cl⁻

[CH₃ (OC₄ H₈)O]₃ SiCH₂ P⁺[(C₃ H₆ O)₂ C₇ H₁₅ ](C₄ H₉)₂ Br⁻

[C₂ H₅ OC(OC₂ H₄)O]₃ SiCH₂ S⁺(CH₃)C₁₈ H₃₇ Cl⁻

[H(OC₂ H₄)₄ O]₃ Si(CH₂)₂ S⁺(C₂ H₄ COOH)C₁₂ H₂₅ Br⁻

[H(OC₂ H₄)₅ O](CH₃)(C₂ H₅ O)SiCH₂ N⁺(CH₃)₂ C₁₂ H₂₅ Cl⁻

[C₁₂ H₂₅ (OC₂ H₄)₃ O](CH₃ O)₂ Si(CH₂)₃ N⁺(C₂ H₅)₂ C₆ H₅ Cl⁻

[H(OC₄ H₈)₆ O](C₂ H₅ O)₂ Si(CH₂)₃ N⁺[(C₂ H₄ O]₁₀ H]₂ C₁₈ H₃₇ Br⁻

[CH₃ CO(OC₂ H₄)₃ O]₂ (C₂ H₅ O)Si(CH₂)₂ N⁺[(C₂ H₄ O)C₂ H₅ ](C₆ H₅ CH₃)₂Cl⁻

[H(OC₂ H₄)₁₂ O](C₄ H₈ O)₂ SiCH₂ N⁺[(C₂ H₄ O)₄ COCH₃ ]₂ C₁₄ H₂₉ Cl⁻

[C₁₆ H₃₃ (OC₂ H₄)₃ O](C₂ H₅) (CH₃ O)SiCh₂ N⁺(0)⁻(CH₃)C₆ H₁₃

[h(oc₃ h₆)₁₂ o](c₂ h₅ o)₂ siCH₂ N⁺(C₂ H₅ COOH) (CH₃)C₁₀ H₂₁ Cl⁻

[C₂ H₅ (OC₂ H₄)₁₄ O]₂ (C₄ H₉ O)Si(CH₂)₃ N⁺(C₄ H₈ OH) (CH₃)C₁₄ H₂₉ Cl⁻

[H(OC₂ H₄)₁₆ O]₂ (CH₃ O)SiCH₂ P⁺(CH₃)₂ C₆ H₄ C₂ H₅ Cl⁻

[C₃ H₇ (OC₂ H₄)₆ O](C₂ H₅) (CH₃ O)SiCH₂ P⁺[(C₂ H₄ O)₈ H]₂ C₈ H₁₇ Br⁻

[CH₃ OC(OC₂ H₄)₂ O]₂ (CH₃ O)Si(CH.sub. 2)₂ P⁺[(C₃ H₆ O)₃ C₂ H₅ ](C₄ H₉)₂Cl⁻

[H(OC₄ H₈)₂ O](C₁₂ H₂₅) (CH₃ O)SiCH₂ P⁺(O)⁻(CH₃)C₆ H₅ 2

[c₁₄ h₂₉ (oc₂ h₄)₆ o](ch₃ o)₂ siCH₂ P⁺(C₃ H₆ COOH)₂ CH₃ Cl⁻

[H(OC₂ H₄)₈ O]₂ (C₄ H₉ O)SiCH₂ P⁺(C₃ H₆ OH)₂ C₂ H₅ Br⁻

[H (OC₂ H₄)₁₀ O]₂ (C₃ H₇ O)SiCH₂ S⁺(CH₃)C₆ H₁₂ C₆ H₅ Cl⁻

[CH₃ (OC₂ H₄)₂₀ O]₃ Si(CH₂)₃ S⁺(C₃ H₆ OH)C₁₆ H₃₃ Br⁻

[H(OC₃ H₆)₁₂ O]₃ Si(CH₂)₂ S⁺(O)^(-C) ₅ H₁₁

[c₁₂ h₂₅ (oc₂ h₄)₄ o]₃ siCH₂ S⁺[(C₂ H₄ O)₂₀ H]CH₃ Br⁻

[H(OC₂ H₄)₁₂ O]₃ Si(CH₂)₃ S⁺[(C₂ H₄ O)C₁₄ H₂₉ ]C₆ H₄ CH₃ Cl⁻

[H(OC₄ H₈)₂ O]₂ (CH₃ O)Si(CH₂)₃ S⁺[(C₂ H₄ O)₄ H]CH₃ Br⁻

[C₁₂ H₂₅ (OC₂ H₄)₆ O](CH₃)(CH₃ O)SiCH₂ S⁺[(C₃ H₆ O)₈ CH₃ ]C₃ H₇ Cl⁻

[CH₃ CO(OC₂ H₄)₃ O](C₂ H₅ O)₂ Si(CH₂)₂ S⁺(C₂ H₄ OH)C₁₂ H₂₅ Cl⁻

[CH₃ (OC₃ H₆)₁₂ O](CH₃ O)₂ SiCH₂ S⁺(C₃ H₆ COOH)CH₂ C₆ H₅ Br⁻

[H(C₂ H₄ O)₆ O](C₁₂ H₂₅)(CH₃ O)SiCH₂ S⁺(O)^(-C) ₁₄ H₂₉

Siloxane oligomers of the organosilanes are formed from the monomers bythe controlled addition of from 1 to 100 equivalents of water,preferably in an inert solvent such as alcohol, tetrahydrofuran, etc. Asused herein, "oligomers" is used to mean a degree of polymerization offrom 2 to 100, preferably 2 to 20. A higher degree of polymerizationadversely affects the ability of the compound to bond itself to ametallic or vitreous surface as discussed below and is for this reasonavoided. Examples of siloxane oligomers having varying degrees ofpolymerization are readily visualized from the above examples oforganosilane monomers.

The above organosilanes are useful when used in a detergent compositionat a level of organosilane to watersoluble organic detergent of from 2:1to 1:10,000. When metallic or vitreous surfaces are washed or rinsedwith a detergent composition containing the above-describedorganosilane, a soil release benefit is imparted to the surface. It istheorized that the positively charged organosilane is attracted to thenegatively charged surface. The silicon atom in the organosilane canthen form a bond with the surface. The presence of the positive chargeon the organosilane is necessary to allow the bonding to take place froma dilute solution as is normally encountered with detergent compositionsand within a reasonable time period. The terminal alkyl groups attachedto the positively charged atom provides the soil release benefits. It isbelieved that the organosilane compound polymerizes on the surface toform a thin coating of the polymer. The coating is responsible forimparting the soil release benefits to the surface. That is, a hardsurface having on it the polymeric coating will be soiled; however, thesoil is not tenaciously bound to the surface by virtue of the coatingand for this reason is easily washed away.

The following examples illustrate the invention.

EXAMPLE I CH₃ O(CH₂ CH₂ O)₂ (OCH₃)₂ Si(CH₂)₃ N⁺(CH₃) (CH₂ CH₂ COO⁻)C₁₈H₃₇

A mixture of 12.0g of gamma-bromopropyltrimethoxysilane and 14.15g ofoctadecylmethylamine are heated at 94-113° C. for 16 hours and thencooled. The resulting tertiary ammonium salt is dissolved in 100 ml ofabsolute ethanol and 0.05 moles of freshly prepared sodium ethoxide in50 ml of ethanol is added. Filtration of the resulting solution andremoval of the solvent yield the tertiary amine,gammamethyloctadecylaminopropyltrimethoxysilane.

A mixture of 22.2g (0.05 mole) of this product and 8.75g of ##STR9## areheated in 78g of methyl carbitol for 18 hr at 130° C. NMR analysis ofthe resulting product indicates complete reaction yielding the expectedzwitterionic silane wherein part of the methoxy on silicon is displacedby a methylcarbitol moiety.

Corresponding organosilanes wherein the nitrogen atom is replaced by aphosphorous atom or a sulfur atom are produced by the above reactionsteps by using octadecylmethylphosphine or octadecylsulfide in place ofthe octadecylmethylamine.

EXAMPLE II C₁₃ H₂₇ O(CH₂ CH₂ O)₆ (OCH₃)₁ SiCH₂ N⁺(CH₃)₂ C₈ H₁₇ Br⁻

A mixture of 20g (0.1 mole) of methylbromomethyldimethoxysilane, 15.7gof octydimethylamine, 46.4g of coconut alcohol ethoxylated with 6 molesof ethylene oxide, and 100 ml. of 2-butanone are refluxed for 12 hours.The 2-butonone is then distilled out of the mixture at atmosphericpressure along with 0.1 moles of methanol to leave the desired product.

EXAMPLE III CH₃ OCH₂ CH₂ O(OCH₃)₂ Si(CH₂)₂ N⁺(CH₂ CH₂ OCOCH₃)₂ C₁₂ H₂₅Br⁻

To 161.5g of vinyltrichlorosilane (commercially available) in 300 ml. ofhexane is added an excess of dry HBr. The reaction flask is sealed andkept for 24 hours, whereupon it is opened and the product is strippedand distilled yielding beta-bromoethyltrichlorosilane.

One-half mole of the beta-bromoethyltrichlorosilane is dissolved in 100ml. of dry hexane and 0.5 moles of betamethoxyethanol is added dropwisewhile the solution is agitated by a nitrogen flush. One hour aftercompletion of the addition, 1.2 moles of methanol is added continuingthe nitrogen flush. After all HCl evolution has ceased, the residue isdistilled yielding

    CH.sub.3 OCH.sub.2 CH.sub.2 O(CH.sub.3 O).sub.2 SiCH.sub.2 CH.sub.2 Br

Two-tenths mole (54.6g) of this product and two-tenths mole (72g) of thediacetate of dodecyldiethanolamine are mixed with 200 ml. ofacetonitrile and refluxed for 12 hours. Removal of the acetonitrileunder reduced pressure yields the desired product.

What is claimed is:
 1. An organosilane having the formula ##STR10## orsiloxane oligomers thereof, wherein x is 2 to 4, m is 1 to 20, Z ishydrogen, an alkyl group containing 1 to 18 carbon atoms or an acylgroup containing 1 to 4 carbon atoms; a is 0 to 2; c is 0 to 2 provideda+c does not exceed 2; R₁ is an alkyl group containing 1 to 4 carbonatoms; R₂ is an alkyl group containing 1 to 18 carbon atoms, b is 1 to3; R₃ is an alkyl, aryl or arylalkyl group containing 1 to 12 carbonatoms, a carboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m, and Z are as defined above, or oxygen provided only one R₃is oxygen and further provided that when R₃ is oxygen there is no X^(-;)R₄ is an alkyl, aryl, or arylalkyl group containing 1 to 22 carbonatoms; X is halide; and Y is nitrogen, phosphorus, or sulfur.
 2. Theorganosilane of claim 1 wherein (a+c) is
 2. 3. The organosilane of claim1 where c is 1 or
 2. 4. The organosilane of claim 1 wherein the siloxaneoligomer has a degree of polymerization of from 2 to
 100. 5. Theorganosilane of claim 1 wherein the degree of polymerization is from 2to
 20. 6. The organosilane of claim 1 wherein the organosilane is amonomer.
 7. The organosilane of claim 1 wherein Z is hydrogen.
 8. Theorganosilane of claim 1 wherein Z is an alkyl group.
 9. The organosilaneof claim 1 wherein Z is an acyl group.
 10. The organosilane of claim 1wherein X is chloride or bromide.
 11. The organosilane of claim 1wherein R₂ is methyl.
 12. The organosilane of claim 1 wherein R₃ is analkyl group containing 1 to 4 carbon atoms.
 13. The organosilane ofclaim 1 wherein R₄ contains 6 to 12 carbon atoms.
 14. The organosilaneof claim 1 having the formula ##STR11##or siloxane oligomers thereof,wherein x is 2 to 4, m is 1 to 20, Z is hydrogen, or alkyl groupcontaining 1 to 18 carbon atoms or an acyl group containing 1 to 4carbon atoms, R₁ is an alkyl group containing 1 to 4 carbon atoms; a is0 to 2; c is 0 to 2 provided a+c does not exceed 2; R₂ is an alkyl groupcontaining 1 to 18 carbon atoms; b is 1 to 3; R₃ is an alkyl, aryl, orarylalkyl group containing 1 to 12 carbon atoms, a carboxy-substitutedalkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

wherein x, m, and Z are as defined above, or oxygen provided only one R₃is oxygen and further provided that when R₃ is oxygen there is no X^(-;)R₄ is an alkyl, aryl or arylalkyl group containing 1 to 22 carbon atoms;and X is halide.